1-Butanol → Butyl cyclopropanesulfonate

Temperature

-10 °C

Cyclopropanesulfonyl chloride (5 g, 35 mmol, 1 eq) was dissolved in an excess BuOH (20 ml), the reaction mixture was cooled at −10° C. and pyridine (5.8 mL, 70 mmol, 2 eq) was slowly added dropwise. The mixture was slowly warmed at room temperature and stirred overnight. The solvent was removed under reduced pressure and the resulting white solid was dissolved in CHCl3. The organic phase was washed with water, brine and dried (MgSO4) and concentrated to give an oil (4.8 g, 24.9 mmol, 71%). 1H NMR (300 MHz, CDCl3): δ 4.25 (t, 2H), 2.46 (m, 1H), 1.74 (m, 2H), 1.45 (m, 2H), 1.25 (dd, 2H), 1.09 (dd, 2H), 0.93 (t, 3H).

1. temperatureThe mixture was slowly warmed at room temperature
2. customThe solvent was removed under reduced pressure
3. dissolutionthe resulting white solid was dissolved in CHCl3
4. washThe organic phase was washed with water, brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated

ORD record

ord-3f0c56fe5db740a786573f8eb5bf5070

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648116B2